Various types of cargo strap winding devices are known in the prior art. However, the previous devices either break or require that the user throw a hook over the trailer before winding up the cargo strap, which is a dangerous task. However, what is needed is trailer cargo strap rolling device for conestoga-style and flatbed trailers, the device including a base that fits into a trailer stake pocket, an inner post member secured into an outer post member with a lock pin, and a winder assembly operated including a sleeve through which a threaded end of a crank handle member is secured and a roller grip member having a receiver end rotatingly attached to the threaded end of the crank handle member and also having a tubular U-shaped support member around which a cargo strap is wound. The crank handle member may be turned either manually or with a wireless drill.